Inhibitory Effects of the Compounds Isolated from Sargassum yezoense on ${\alpha}$-Glucosidase and Oxidative Stress

왜모자반 (Sargassum yezoense)에서 분리한 화합물의 ${\alpha}$-glucosidase 및 산화스트레스 억제효과

  • Lee, Eun-Ha (Natural Products Research Center, Korea Institute of Science and Technology (KIST) Gangneung Institute) ;
  • Ham, Jung-Yeob (Natural Products Research Center, Korea Institute of Science and Technology (KIST) Gangneung Institute) ;
  • Ahn, Hong-Ryul (Natural Products Research Center, Korea Institute of Science and Technology (KIST) Gangneung Institute) ;
  • Kim, Min-Chul (Natural Products Research Center, Korea Institute of Science and Technology (KIST) Gangneung Institute) ;
  • Kim, Chul-Young (Natural Products Research Center, Korea Institute of Science and Technology (KIST) Gangneung Institute) ;
  • Pan, Cheol-Ho (Natural Products Research Center, Korea Institute of Science and Technology (KIST) Gangneung Institute) ;
  • Um, Byung-Hun (Natural Products Research Center, Korea Institute of Science and Technology (KIST) Gangneung Institute) ;
  • Jung, Sang-Hoon (Natural Products Research Center, Korea Institute of Science and Technology (KIST) Gangneung Institute)
  • 이은하 (한국과학기술연구원 강릉분원) ;
  • 함정엽 (한국과학기술연구원 강릉분원) ;
  • 안홍열 (한국과학기술연구원 강릉분원) ;
  • 김민철 (한국과학기술연구원 강릉분원) ;
  • 김철영 (한국과학기술연구원 강릉분원) ;
  • 판철호 (한국과학기술연구원 강릉분원) ;
  • 엄병헌 (한국과학기술연구원 강릉분원) ;
  • 정상훈 (한국과학기술연구원 강릉분원)
  • Published : 2009.06.30

Abstract

We examined ethanol extracts prepared from the Korean marine algae belonging to the Sargassaceae family for their inhibitory effects on ${\alpha}$-glucosidase activity and free radicals in vitro. Among five marine algae, the extracts of Sargassum yezoense were found to possess strongly ${\alpha}$-glucosidase inhibition and free radicals scavenging activities. Two compounds were isolated via bioactivity guided isolation and tested for their effects on ${\alpha}$-glucosidase, DPPH, $ABTS^{+}$ and $Photochem^{(R)}$ analysis. Their chemical structures were elucidated by spectral analysis and direct comparison with authentic compounds; their structures were identified as sargaquinoic acid (1) and sargahydroquinoic acid (2). The inhibitory effects of compound 1 and 2 ($IC_{50}$ value:14.2 and 12.8 ${\mu}M$, respectively) on ${\alpha}$-glucosidase were more potent that of deoxynojirimycin as a positive control ($IC_{50}$ value:18.0 ${\mu}M$). All compounds displayed antioxidative activity which was measured by DPPH, $ABTS^{+}$ and $Photochem^{(R)}$ apparatus.

Keywords

References

  1. Moller, D. E. (2001) New drug targets for type 2 diabetes and the metabolic syndrome. Nature 414: 821-827 https://doi.org/10.1038/414821a
  2. 임중인. (2003) 당뇨병치료제의 최근 연구동향. 보건산업기술동향
  3. Lebovitz, H. E. (1992) Oral antidiabetic agents. The emergence of $\alpha$-glucosidase inhibitors. Drugs 44 Suppl 3: 21-28
  4. Nakai, M., Kageyama, N., Nakahara, K. and Miki, W. (2006) Phlorotannins as radical scavengers from the extract of Sargassum ringgoldianum. Mar. Biotechnol. (NY) 8: 409-414 https://doi.org/10.1007/s10126-005-6168-9
  5. Reddy, P. and Urban, S. (2009) Meroditerpenoids from the southern Australian marine brown alga Sargassum fallax. Phytochemistry 70: 250-255 https://doi.org/10.1016/j.phytochem.2008.12.007
  6. Jung, M., Jang, K. H., Kim, B., Lee, B. H., Choi, B. W., Oh, K. B. and Shin, J. (2008) Meroditerpenoids from the brown alga Sargassum siliquastrum. J. Nat. Prod. 71: 1714-1719 https://doi.org/10.1021/np800321y
  7. Seo, Y., Park, K. E., Kim, Y. A., Lee, H. J., Yoo, J. S., Ahn, J. W. and Lee, B. J. (2006) Isolation of tetraprenyltoluquinols from the brown alga Sargassum thunbergii. Chem. Pharm. Bull. (Tokyo) 54: 1730-1733 https://doi.org/10.1248/cpb.54.1730
  8. Kim, S. N., Choi, H. Y., Lee, W., Park, G. M., Shin, W. S. and Kim, Y. K. (2008) Sargaquinoic acid and sargahydroquinoic acid from Sargassum yezoense stimulate adipocyte differentiation through PPARalpha/gamma activation in 3T3-L1 cells. FEBS Lett. 582: 3465-3472 https://doi.org/10.1016/j.febslet.2008.09.011
  9. Lam, S. H., Chen, J. M., Kang, C. J., Chen, C. H. and Lee, S. S. (2008) alpha-Glucosidase inhibitors from the seeds of Syagrus romanzoffiana. Phytochemistry 69: 1173-1178 https://doi.org/10.1016/j.phytochem.2007.12.004
  10. Cao, G., Sofic, E. and Prior, R. L. (1997) Antioxidant and prooxidant behavior of flavonoids: structure-activity relationships. Free Radic. Biol. Med. 22: 749-760 https://doi.org/10.1016/S0891-5849(96)00351-6
  11. Re, R., Pellegrini, N., Proteggente, A., Pannala, A., Yang, M. and Rice-Evans, C. (1999) Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radic. Biol. Med. 26: 1231-1237 https://doi.org/10.1016/S0891-5849(98)00315-3
  12. Lee, E. H., Song, D. G., Lee, J. Y., Pan, C. H., Um, B. H. and Jung, S. H. (2008) Inhibitory effect of the compounds isolated from Rhus verniciflua on aldose reductase and advanced glycation endproducts. Biol. Pharm. Bull. 31: 1626-1630 https://doi.org/10.1248/bpb.31.1626
  13. Baynes, J. W. and Thorpe, S. R. (1999) Role of oxidative stress in diabetic complications: a new perspective on an old paradigm. Diabetes 48: 1-9 https://doi.org/10.2337/diabetes.48.1.1
  14. Sato, Y., Hotta, N., Sakamoto, N., Matsuoka, S., Ohishi, N. and Yagi, K. (1979) Lipid peroxide level in plasma of diabetic patients. Biochem. Med. 21: 104-107 https://doi.org/10.1016/0006-2944(79)90061-9